GB1447218A - Phenoxyalkanol derivatives and a process for their preparation - Google Patents

Phenoxyalkanol derivatives and a process for their preparation

Info

Publication number
GB1447218A
GB1447218A GB1274575A GB1274575A GB1447218A GB 1447218 A GB1447218 A GB 1447218A GB 1274575 A GB1274575 A GB 1274575A GB 1274575 A GB1274575 A GB 1274575A GB 1447218 A GB1447218 A GB 1447218A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
group
hal
alkanoyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1274575A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of GB1447218A publication Critical patent/GB1447218A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Quinoline Compounds (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1447218 Phenoxy alkanols and esters thereof MERCK PATENT GmbH 26 March 1975 [2 April 1974] 12745/75 Heading C2C Novel compounds I: wherein R<SP>1</SP> is H or CH 3 ; R<SP>2</SP> is CH 3 or C 6 H 5 ; R<SP>3</SP> is 4-halo-phenoxymethyl, 1,2,3,4-tetrahydro-1- naphthyl, 1-pyrryl, piperidino, isoindolino, 1,2,3,4-tetrahydroquinolino, 1,2,3,4-tetrahydro- 1 - R<SP>5</SP> - 4 - quinolyl, 4 - chromanyl, 4 - thiochromanyl, or, if R<SP>1</SP> and R<SP>2</SP> are not both CH 3 , R<SP>3</SP> may also be hal, phenyl, 4-hal-phenyl or 4- hal-phenoxy; R<SP>4</SP> is H or alkanoyl with 2 to 4 carbon atoms; R<SP>5</SP> is H or CH 3 and hal is F, Cl or Br; and their physiologically acceptable acid addition salts, are prepared by (i) reacting a phenol II: (which may be partly or wholly in the form of a phenolate) with a compound of formula X-CR<SP>1</SP>R<SP>2</SP>-CH 2 OR<SP>4</SP> in which X is Cl, Br, I, OH or an esterified OH group provided that when X is OH, R<SP>4</SP> is alkanoyl with 2 to 4 carbon atoms, to form a compound of Formula I, or (ii) reducing a compound of Formula IV: wherein Y is a free or functionally modified COOH group, a free or functionally modified CHO group, or a CH 2 OCH 2 C 6 H 5 group, to form a compound of Formula I, or (iii) treating a compound of Formula IV above wherein Y is a CH 2 hal group or an esterified or etherified CH 2 OH group, with a solvolysing agent, to form a compound of Formula I, or (iv) diazotizing a compound of Formula IV above wherein Y is an aminomethyl group, and reacting the resulting diazonium compound with a compound of formula R<SP>4</SP>-OH wherein R<SP>4</SP> has the abovestated meaning, to form a compound of Formula I, and, if desired, converting a compound I into another compound I by saponifying an alkanoyloxy group therein and/or esterifying a hydroxyl group therein. A resulting compound I may be reacted with an acid to form a physiologically acceptable acid addition salt. Pharmaceutical compositions for oral, parenteral or topical administration comprise a compound of the invention together with a pharmaceutical carrier. The compositions are useful for lowering cholesterol, triglyceride and uric acid levels and for inducing liver enzymes.
GB1274575A 1974-04-02 1975-03-26 Phenoxyalkanol derivatives and a process for their preparation Expired GB1447218A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2415867A DE2415867A1 (en) 1974-04-02 1974-04-02 PHENOXY ALCANOL DERIVATIVES AND THE PROCESS FOR THEIR PRODUCTION

Publications (1)

Publication Number Publication Date
GB1447218A true GB1447218A (en) 1976-08-25

Family

ID=5911908

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1274575A Expired GB1447218A (en) 1974-04-02 1975-03-26 Phenoxyalkanol derivatives and a process for their preparation

Country Status (8)

Country Link
JP (1) JPS50137937A (en)
AT (1) AT355021B (en)
DE (1) DE2415867A1 (en)
ES (1) ES436218A1 (en)
FR (1) FR2265356B1 (en)
GB (1) GB1447218A (en)
NL (1) NL7503854A (en)
SE (1) SE7503632L (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1512189A (en) * 1975-10-29 1978-05-24 Ishihara Mining & Chemical Co Herbicidal composition and method of use thereof
DE2611695A1 (en) * 1976-03-19 1977-09-29 Hoechst Ag HERBICIDAL AGENTS
NZ213986A (en) * 1984-10-30 1989-07-27 Usv Pharma Corp Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such
BR0308537A (en) * 2002-03-20 2005-02-09 Metabolex Inc Compound, composition, and methods for treating type 2 diabetes and hyperuricemia, modulating insulin resistance and alleviating hyperlipidemia in an individual and prodrug agent
RU2686987C2 (en) * 2014-12-30 2019-05-06 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Picolinamides as fungicides

Also Published As

Publication number Publication date
ES436218A1 (en) 1977-04-01
ATA247475A (en) 1979-07-15
AT355021B (en) 1980-02-11
FR2265356A1 (en) 1975-10-24
DE2415867A1 (en) 1975-10-09
JPS50137937A (en) 1975-11-01
NL7503854A (en) 1975-10-06
FR2265356B1 (en) 1978-12-22
SE7503632L (en) 1975-10-03

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee